Passwords can be used to gain access to specific data, an account, a computer system or a protected space. A single user may have multiple accounts that are protected by passwords. Research shows that users tend to keep same or similar passwords for different accounts with little differences. Once a single password becomes known, a number of accounts can be compromised. This paper deals with password security, a close look at what goes into making a password strong and the difficulty involved in breaking a password. The following sections discuss related work and prove graphically and mathematically the different aspects of password securities, overlooked vulnerabilities and the importance of passwords that are widely ignored. This work describes tests that were carried out to evaluate the resistance of passwords of varying strength against brute force attacks. It also discusses overlooked parameters such as entropy and how it ties in to password strength. This work also discusses the password composition enforcement of different popular websites and then presents a system designed to provide an adaptive and effective measure of password strength. This paper contributes toward minimizing the risk posed by those seeking to expose sensitive digital data. It provides solutions for making password breaking more difficult as well as convinces users to choose and set hard-to-break passwords.